# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 18 08:12:29 2020
#   Inital geometry file: a 139 line input string
#   Ligand name: N-(4-{[1-methyl-3-(1-methyl-1H-pyrazol-4-yl)-1H-indol-5-yl]oxy}phenyl)-L-prolinamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cn1cc(cn1)c2cn(C)c3ccc(Oc4ccc(NC(=O)[C@@H]5CCCN5)cc4)cc23
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 8V1  8V1  N-(4-{[1-methyl-3-(1-methyl-1H-pyrazol-4-yl)-1H-indol-5-yl]oxy}phenyl)-L-prolinamide  ligand  56  31  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_8V1
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 8V1  O1    O  O     0  -0.461   5.4281   0.2427   1.3220
 8V1  C15   C  C     0   0.530   5.3779   0.4504   0.1250
 8V1  C16   C  CH1   0  -0.249   6.4767   0.0261  -0.8372
 8V1  N2    N  NH1   0  -0.577   7.7384  -0.1794  -0.1435
 8V1  C19   C  CH2   0  -0.317   7.9271  -1.6222  -0.0369
 8V1  C18   C  CH2   0  -0.454   7.3176  -2.2034  -1.3105
 8V1  C17   C  CH2   0  -0.477   6.0780  -1.3309  -1.4994
 8V1  N1    N  NH1   0  -0.736   4.3192   1.0279  -0.5010
 8V1  C12   C  CR6   0   0.349   3.0647   1.3455   0.0397
 8V1  C11   C  CR16  0  -0.293   2.8591   1.6681   1.3811
 8V1  C10   C  CR16  0  -0.328   1.5873   1.9758   1.8367
 8V1  C13   C  CR16  0  -0.327   1.9710   1.3637  -0.8226
 8V1  C14   C  CR16  0  -0.331   0.6997   1.6837  -0.3731
 8V1  C9    C  CR6   0   0.351   0.5024   1.9848   0.9687
 8V1  O     O  O2    0  -0.521  -0.7058   2.3219   1.5009
 8V1  C7    C  CR6   0   0.308  -1.8493   2.0496   0.7827
 8V1  C6    C  CR16  0  -0.338  -2.5151   3.1191   0.1695
 8V1  C5    C  CR16  0  -0.308  -3.7012   2.9110  -0.5080
 8V1  C4    C  CR56  0   0.373  -4.1930   1.6095  -0.5703
 8V1  N     N  NR5   0  -0.521  -5.3323   1.1283  -1.1493
 8V1  C     C  CH3   0  -0.529  -6.2781   1.9114  -1.9051
 8V1  C8    C  CR16  0  -0.452  -2.3263   0.7571   0.7223
 8V1  C3    C  CR56  0   0.031  -3.5149   0.5224   0.0250
 8V1  C2    C  CR5   0   0.005  -4.2986  -0.6492  -0.2321
 8V1  C1    C  CR15  0  -0.092  -5.3847  -0.2208  -0.9512
 8V1  C20   C  CR5   0  -0.176  -4.0114  -2.0111   0.1846
 8V1  C22   C  CR15  0  -0.009  -4.9074  -3.0003   0.5444
 8V1  N4    N  NR5   0  -0.263  -4.1892  -4.0970   0.8418
 8V1  C23   C  CH3   0  -0.506  -4.6896  -5.3910   1.2388
 8V1  N3    N  N     0  -0.283  -2.8843  -3.8993   0.7052
 8V1  C21   C  CR15  0  -0.124  -2.7589  -2.6453   0.3102
 8V1  H16   H  HCH1  0   0.278   6.5977   0.7999  -1.5996
 8V1  H1    H  HNH1  0   0.411   4.3839   1.1061  -1.5052
 8V1  H2    H  HNH1  0   0.354   8.4818   0.2040  -0.7117
 8V1  H171  H  HCH2  0   0.244   5.2220  -1.7814  -0.9913
 8V1  H172  H  HCH2  0   0.253   5.7970  -1.2017  -2.5440
 8V1  H191  H  HCH2  0   0.239   8.9824  -1.8612   0.0948
 8V1  H192  H  HCH2  0   0.222   7.3924  -1.9963   0.8407
 8V1  H181  H  HCH2  0   0.229   8.0116  -2.0780  -2.1449
 8V1  H182  H  HCH2  0   0.236   7.0763  -3.2641  -1.2322
 8V1  H11   H  HCR6  0   0.274   3.6787   1.6845   2.0808
 8V1  H13   H  HCR6  0   0.273   2.1085   1.1223  -1.8699
 8V1  H10   H  HCR6  0   0.269   1.4394   2.2174   2.8818
 8V1  H14   H  HCR6  0   0.279  -0.1210   1.6873  -1.0776
 8V1  H6    H  HCR6  0   0.266  -2.0986   4.1155   0.2415
 8V1  H8    H  HCR6  0   0.258  -1.7930  -0.0462   1.2161
 8V1  H5    H  HCR6  0   0.272  -4.2188   3.7402  -0.9728
 8V1  HC1   H  HCH3  0   0.254  -5.8527   2.2390  -2.8539
 8V1  HC2   H  HCH3  0   0.265  -7.1592   1.3093  -2.1090
 8V1  HC3   H  HCH3  0   0.255  -6.5874   2.7887  -1.3385
 8V1  HA    H  HCR5  0   0.287  -6.2041  -0.7969  -1.3541
 8V1  H22   H  HCR5  0   0.285  -5.9833  -2.9883   0.6164
 8V1  H21   H  HCR5  0   0.249  -1.7799  -2.2346   0.1131
 8V1  H231  H  HCH3  0   0.258  -4.5511  -6.1195   0.4416
 8V1  H232  H  HCH3  0   0.261  -4.1675  -5.7326   2.1294
 8V1  H233  H  HCH3  0   0.258  -5.7496  -5.3091   1.4610

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 8V1  O1   C15   double    1.216  0.020  1.216
 8V1  C15  C16   single    1.521  0.020  1.521
 8V1  C15  N1    single    1.359  0.020  1.359
 8V1  C16  N2    single    1.454  0.020  1.454
 8V1  C16  C17   single    1.562  0.020  1.562
 8V1  N2   C19   single    1.459  0.020  1.459
 8V1  C19  C18   single    1.527  0.020  1.527
 8V1  C18  C17   single    1.528  0.020  1.528
 8V1  N1   C12   single    1.403  0.020  1.403
 8V1  C12  C11   aromatic  1.395  0.020  1.395
 8V1  C12  C13   aromatic  1.393  0.020  1.393
 8V1  C11  C10   aromatic  1.386  0.020  1.386
 8V1  C10  C9    aromatic  1.389  0.020  1.389
 8V1  C13  C14   aromatic  1.386  0.020  1.386
 8V1  C14  C9    aromatic  1.389  0.020  1.389
 8V1  C9   O     single    1.363  0.020  1.363
 8V1  O    C7    single    1.377  0.020  1.377
 8V1  C7   C6    aromatic  1.401  0.020  1.401
 8V1  C7   C8    aromatic  1.379  0.020  1.379
 8V1  C6   C5    aromatic  1.382  0.020  1.382
 8V1  C5   C4    aromatic  1.393  0.020  1.393
 8V1  C4   N     aromatic  1.366  0.020  1.366
 8V1  C4   C3    aromatic  1.413  0.020  1.413
 8V1  N    C     single    1.442  0.020  1.442
 8V1  N    C1    aromatic  1.365  0.020  1.365
 8V1  C8   C3    aromatic  1.398  0.020  1.398
 8V1  C3   C2    aromatic  1.433  0.020  1.433
 8V1  C2   C1    aromatic  1.371  0.020  1.371
 8V1  C2   C20   single    1.453  0.020  1.453
 8V1  C20  C22   aromatic  1.382  0.020  1.382
 8V1  C20  C21   aromatic  1.410  0.020  1.410
 8V1  C22  N4    aromatic  1.344  0.020  1.344
 8V1  N4   C23   single    1.443  0.020  1.443
 8V1  N4   N3    aromatic  1.327  0.020  1.327
 8V1  N3   C21   aromatic  1.321  0.020  1.321
 8V1  C16  H16   single    0.970  0.020  1.090
 8V1  N1   H1    single    0.860  0.020  1.020
 8V1  N2   H2    single    0.890  0.020  1.040
 8V1  C17  H171  single    0.970  0.020  1.090
 8V1  C17  H172  single    0.970  0.020  1.090
 8V1  C19  H191  single    0.970  0.020  1.090
 8V1  C19  H192  single    0.970  0.020  1.090
 8V1  C18  H181  single    0.970  0.020  1.090
 8V1  C18  H182  single    0.970  0.020  1.090
 8V1  C11  H11   single    0.930  0.020  1.080
 8V1  C13  H13   single    0.930  0.020  1.080
 8V1  C10  H10   single    0.930  0.020  1.080
 8V1  C14  H14   single    0.930  0.020  1.080
 8V1  C6   H6    single    0.930  0.020  1.080
 8V1  C8   H8    single    0.930  0.020  1.080
 8V1  C5   H5    single    0.930  0.020  1.080
 8V1  C    HC1   single    0.970  0.020  1.090
 8V1  C    HC2   single    0.970  0.020  1.090
 8V1  C    HC3   single    0.970  0.020  1.090
 8V1  C1   HA    single    0.930  0.020  1.080
 8V1  C22  H22   single    0.930  0.020  1.080
 8V1  C21  H21   single    0.930  0.020  1.080
 8V1  C23  H231  single    0.970  0.020  1.090
 8V1  C23  H232  single    0.970  0.020  1.090
 8V1  C23  H233  single    0.970  0.020  1.090

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 8V1  N1    C15  C16   112.95  3.000
 8V1  N1    C15  O1    123.94  3.000
 8V1  C16   C15  O1    123.05  3.000
 8V1  H16   C16  C17   110.35  3.000
 8V1  H16   C16  N2    109.67  3.000
 8V1  C17   C16  N2    107.51  3.000
 8V1  H16   C16  C15   108.89  3.000
 8V1  C17   C16  C15   109.04  3.000
 8V1  N2    C16  C15   111.37  3.000
 8V1  H2    N2   C19   108.72  3.000
 8V1  H2    N2   C16   108.43  3.000
 8V1  C19   N2   C16   106.67  3.000
 8V1  H192  C19  H191  107.54  3.000
 8V1  H192  C19  C18   110.12  3.000
 8V1  H191  C19  C18   113.81  3.000
 8V1  H192  C19  N2    109.49  3.000
 8V1  H191  C19  N2    110.54  3.000
 8V1  C18   C19  N2    105.30  3.000
 8V1  H182  C18  H181  107.88  3.000
 8V1  H182  C18  C17   112.63  3.000
 8V1  H181  C18  C17   110.82  3.000
 8V1  H182  C18  C19   113.49  3.000
 8V1  H181  C18  C19   109.87  3.000
 8V1  C17   C18  C19   102.10  3.000
 8V1  H172  C17  H171  107.02  3.000
 8V1  H172  C17  C18   113.31  3.000
 8V1  H171  C17  C18   110.04  3.000
 8V1  H172  C17  C16   111.67  3.000
 8V1  H171  C17  C16   111.17  3.000
 8V1  C18   C17  C16   103.69  3.000
 8V1  H1    N1   C12   115.05  3.000
 8V1  H1    N1   C15   116.19  3.000
 8V1  C12   N1   C15   127.99  3.000
 8V1  C13   C12  C11   118.46  3.000
 8V1  C13   C12  N1    117.82  3.000
 8V1  C11   C12  N1    123.71  3.000
 8V1  H11   C11  C10   118.76  3.000
 8V1  H11   C11  C12   121.04  3.000
 8V1  C10   C11  C12   120.19  3.000
 8V1  H10   C10  C9    119.65  3.000
 8V1  H10   C10  C11   119.50  3.000
 8V1  C9    C10  C11   120.85  3.000
 8V1  H13   C13  C14   118.77  3.000
 8V1  H13   C13  C12   119.72  3.000
 8V1  C14   C13  C12   121.50  3.000
 8V1  H14   C14  C9    121.37  3.000
 8V1  H14   C14  C13   119.05  3.000
 8V1  C9    C14  C13   119.58  3.000
 8V1  O     C9   C14   123.84  3.000
 8V1  O     C9   C10   116.74  3.000
 8V1  C14   C9   C10   119.41  3.000
 8V1  C7    O    C9    118.92  3.000
 8V1  C8    C7   C6    122.13  3.000
 8V1  C8    C7   O     119.69  3.000
 8V1  C6    C7   O     118.15  3.000
 8V1  H6    C6   C5    120.11  3.000
 8V1  H6    C6   C7    119.39  3.000
 8V1  C5    C6   C7    120.50  3.000
 8V1  H5    C5   C4    121.86  3.000
 8V1  H5    C5   C6    120.38  3.000
 8V1  C4    C5   C6    117.76  3.000
 8V1  C3    C4   N     107.93  3.000
 8V1  C3    C4   C5    122.05  3.000
 8V1  N     C4   C5    130.01  3.000
 8V1  C1    N    C     126.00  3.000
 8V1  C1    N    C4    108.60  3.000
 8V1  C     N    C4    125.32  3.000
 8V1  HC3   C    HC2   108.28  3.000
 8V1  HC3   C    HC1   108.75  3.000
 8V1  HC2   C    HC1   108.64  3.000
 8V1  HC3   C    N     110.55  3.000
 8V1  HC2   C    N     109.23  3.000
 8V1  HC1   C    N     111.31  3.000
 8V1  H8    C8   C3    121.43  3.000
 8V1  H8    C8   C7    120.31  3.000
 8V1  C3    C8   C7    118.25  3.000
 8V1  C2    C3   C8    133.79  3.000
 8V1  C2    C3   C4    106.92  3.000
 8V1  C8    C3   C4    119.28  3.000
 8V1  C20   C2   C1    126.86  3.000
 8V1  C20   C2   C3    127.36  3.000
 8V1  C1    C2   C3    105.78  3.000
 8V1  HA    C1   C2    129.06  3.000
 8V1  HA    C1   N     120.16  3.000
 8V1  C2    C1   N     110.77  3.000
 8V1  C21   C20  C22   103.35  3.000
 8V1  C21   C20  C2    128.53  3.000
 8V1  C22   C20  C2    128.12  3.000
 8V1  H22   C22  N4    121.83  3.000
 8V1  H22   C22  C20   131.00  3.000
 8V1  N4    C22  C20   107.16  3.000
 8V1  N3    N4   C23   120.20  3.000
 8V1  N3    N4   C22   112.40  3.000
 8V1  C23   N4   C22   127.39  3.000
 8V1  H233  C23  H232  108.95  3.000
 8V1  H233  C23  H231  108.93  3.000
 8V1  H232  C23  H231  109.17  3.000
 8V1  H233  C23  N4    109.09  3.000
 8V1  H232  C23  N4    109.90  3.000
 8V1  H231  C23  N4    110.76  3.000
 8V1  C21   N3   N4    105.40  3.000
 8V1  H21   C21  N3    120.12  3.000
 8V1  H21   C21  C20   128.19  3.000
 8V1  N3    C21  C20   111.68  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 8V1  CONST_01  C9    C10  C11  C12     0.00   0.0  0
 8V1  CONST_02  C9    C14  C13  C12     0.00   0.0  0
 8V1  CONST_03  C14   C13  C12  C11     0.00   0.0  0
 8V1  CONST_04  C14   C9   C10  C11     0.00   0.0  0
 8V1  CONST_05  C13   C12  C11  C10     0.00   0.0  0
 8V1  CONST_06  C13   C14  C9   C10     0.00   0.0  0
 8V1  CONST_07  C4    C5   C6   C7      0.00   0.0  0
 8V1  CONST_08  C4    C3   C8   C7      0.00   0.0  0
 8V1  CONST_09  C2    C3   C8   C7    180.00   0.0  0
 8V1  CONST_10  C3    C8   C7   C6      0.00   0.0  0
 8V1  CONST_11  N     C4   C5   C6    180.00   0.0  0
 8V1  CONST_12  C3    C4   C5   C6      0.00   0.0  0
 8V1  CONST_13  C8    C7   C6   C5      0.00   0.0  0
 8V1  CONST_14  C1    N    C4   C5    180.00   0.0  0
 8V1  CONST_15  C8    C3   C4   C5      0.00   0.0  0
 8V1  CONST_16  C2    C3   C4   C5    180.00   0.0  0
 8V1  CONST_17  C2    C1   N    C4      0.00   0.0  0
 8V1  CONST_18  C1    C2   C3   C4      0.00   0.0  0
 8V1  CONST_19  C20   C2   C3   C4    180.00   0.0  0
 8V1  CONST_20  C8    C3   C4   N     180.00   0.0  0
 8V1  CONST_21  C2    C3   C4   N       0.00   0.0  0
 8V1  CONST_22  C3    C2   C1   N       0.00   0.0  0
 8V1  CONST_23  C20   C2   C1   N     180.00   0.0  0
 8V1  CONST_24  C1    C2   C3   C8    180.00   0.0  0
 8V1  CONST_25  C20   C2   C3   C8      0.00   0.0  0
 8V1  CONST_26  C1    N    C4   C3      0.00   0.0  0
 8V1  CONST_29  N4    C22  C20  C2    180.00   0.0  0
 8V1  CONST_30  N3    C21  C20  C2    180.00   0.0  0
 8V1  CONST_33  N3    N4   C22  C20     0.00   0.0  0
 8V1  CONST_34  N4    N3   C21  C20     0.00   0.0  0
 8V1  CONST_35  N3    C21  C20  C22     0.00   0.0  0
 8V1  CONST_36  C21   N3   N4   C22     0.00   0.0  0
 8V1  CONST_37  C21   C20  C22  N4      0.00   0.0  0
 8V1  CONST_38  C10   C11  C12  N1    180.00   0.0  0
 8V1  CONST_39  C14   C13  C12  N1    180.00   0.0  0
 8V1  CONST_40  O     C9   C10  C11   180.00   0.0  0
 8V1  CONST_41  O     C9   C14  C13   180.00   0.0  0
 8V1  CONST_42  C5    C6   C7   O     180.00   0.0  0
 8V1  CONST_43  C3    C8   C7   O     180.00   0.0  0
 8V1  CONST_44  C     N    C4   C5      0.00   0.0  0
 8V1  CONST_45  C3    C4   N    C     180.00   0.0  0
 8V1  CONST_46  C2    C1   N    C     180.00   0.0  0
 8V1  CONST_47  C23   N4   C22  C20   180.00   0.0  0
 8V1  CONST_48  C21   N3   N4   C23   180.00   0.0  0
 8V1  CONST_49  H10   C10  C11  C12   180.00   0.0  0
 8V1  CONST_50  H14   C14  C13  C12   180.00   0.0  0
 8V1  CONST_51  H13   C13  C12  C11   180.00   0.0  0
 8V1  CONST_52  H11   C11  C12  C13   180.00   0.0  0
 8V1  CONST_53  H5    C5   C6   C7    180.00   0.0  0
 8V1  CONST_54  H8    C8   C7   C6    180.00   0.0  0
 8V1  CONST_55  H6    C6   C5   C4    180.00   0.0  0
 8V1  CONST_56  HA    C1   N    C4    180.00   0.0  0
 8V1  CONST_57  H22   C22  C20  C2      0.00   0.0  0
 8V1  CONST_58  H21   C21  C20  C2      0.00   0.0  0
 8V1  CONST_59  C12   N1   C15  C16   180.00   0.0  0
 8V1  CONST_63  C12   N1   C15  O1      0.00   0.0  0
 8V1  Var_01    C18   C19  N2   C16    34.01  30.0  1
 8V1  Var_02    C19   C18  C17  C16    28.36  30.0  1
 8V1  Var_03    C17   C18  C19  N2    -38.89  30.0  1
 8V1  Var_04    C6    C7   O    C9   -105.88  30.0  2
 8V1  Var_05    HC1   C    N    C4     68.99  30.0  2
 8V1  Var_06    H231  C23  N4   C22   108.57  30.0  2

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 8V1  chir_01  C16  C15  N2  C17  negativ

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 8V1  plan-1  C2   0.020
 8V1  plan-1  C20  0.020
 8V1  plan-1  C22  0.020
 8V1  plan-1  N4   0.020
 8V1  plan-1  C23  0.020
 8V1  plan-1  N3   0.020
 8V1  plan-1  C21  0.020
 8V1  plan-1  H22  0.020
 8V1  plan-1  H21  0.020
 8V1  plan-2  N1   0.020
 8V1  plan-2  C12  0.020
 8V1  plan-2  C11  0.020
 8V1  plan-2  C10  0.020
 8V1  plan-2  C13  0.020
 8V1  plan-2  C14  0.020
 8V1  plan-2  C9   0.020
 8V1  plan-2  O    0.020
 8V1  plan-2  H11  0.020
 8V1  plan-2  H13  0.020
 8V1  plan-2  H10  0.020
 8V1  plan-2  H14  0.020
 8V1  plan-3  O    0.020
 8V1  plan-3  C7   0.020
 8V1  plan-3  C6   0.020
 8V1  plan-3  C5   0.020
 8V1  plan-3  C4   0.020
 8V1  plan-3  N    0.020
 8V1  plan-3  C    0.020
 8V1  plan-3  C8   0.020
 8V1  plan-3  C3   0.020
 8V1  plan-3  C2   0.020
 8V1  plan-3  C1   0.020
 8V1  plan-3  C20  0.020
 8V1  plan-3  H6   0.020
 8V1  plan-3  H8   0.020
 8V1  plan-3  H5   0.020
 8V1  plan-3  HA   0.020
 8V1  plan-4  O1   0.020
 8V1  plan-4  C15  0.020
 8V1  plan-4  C16  0.020
 8V1  plan-4  N1   0.020
 8V1  plan-4  C12  0.020
 8V1  plan-4  H1   0.020

